With internationals rules constantly changing, it is hard to know exactly what kinds of Caribbean travel documents you need when leaving on vacation. Ever country has specific rules and regulations, so you should check ahead by calling the airport, but in general, you’ll need ID and a passport at the very least to fly into a foreign country or foreign territory.
First and foremost, no matter what documentation you have, travel to Cuba is illegal for most United States citizens. Cuba is under a strict communist dictatorship rule, and United States citizens risk their lives by going there. The only people allowed to travel to Cuba are special government officials with certain clearances. Traveling to Cuba by going to another country, like Canada, is also illegal. You can be caught quite easily doing this because the U.S. customs officials will see the Cuban stamp in your passport. It is smarter and safer just to avoid traveling to Cuba, because you will be less likely to get hurt while in the Caribbean and less likely to face charges when entering the United States to get home.
For most Caribbean countries, you will need a passport to travel from the United States into the country. The Caribbean is not a country on its own—the region is actually made up for number of small island countries and European territories. Therefore, every time you enter a new country, you will need to present your passport to be stamped. Regardless of if you need a passport by the island’s law or not, you will need a passport to reenter the United States. If you lose your passport or otherwise find yourself without a passport in a foreign country, contact the airlines immediately to find out what to do.
In some Caribbean countries, you will also need to present your airplane ticket showing that you have a ticket to return home or a ticket to fly on to another country. Immigration is a problem, and if you have not figured out when you’re going to leave, some countries will not let you leave the airport at all. Make sure you have a return or forward flight, regardless of where you go.
When traveling, keep your documentation, tickets, and identification in a safe place that is quickly accessible. Remember that your luggage may arrive long after you actually get to the Caribbean, so keep everything on your person instead. It is a good idea to use a small outside pocket to carry this or to have one person from the family in charge of all of the information in order to prevent it from getting lost.